diff --git a/airflow-core/src/airflow/callbacks/callback_requests.py b/airflow-core/src/airflow/callbacks/callback_requests.py
index ce48438f0e70a..2573c0d89bbde 100644
--- a/airflow-core/src/airflow/callbacks/callback_requests.py
+++ b/airflow-core/src/airflow/callbacks/callback_requests.py
@@ -46,6 +46,12 @@ class BaseCallbackRequest(BaseModel):
     """File Path to use to run the callback"""
     bundle_name: str
     bundle_version: str | None
+    version_data: dict[str, Any] | None = None
+    """Optional structured metadata for the pinned bundle version (e.g. an S3 object manifest).
+
+    Populated only for pinned runs so the callback initializes the bundle against the same
+    version the task ran with; ``None`` for unpinned runs.
+    """
     msg: str | None = None
     """Additional Message that can be used for logging to determine failure/task heartbeat timeout"""
 
diff --git a/airflow-core/src/airflow/dag_processing/manager.py b/airflow-core/src/airflow/dag_processing/manager.py
index b2428985a6506..f41883edf31fd 100644
--- a/airflow-core/src/airflow/dag_processing/manager.py
+++ b/airflow-core/src/airflow/dag_processing/manager.py
@@ -705,7 +705,11 @@ def prepare_callback_bundle(self, request: CallbackRequest) -> BaseDagBundle | N
         Override to source the bundle from an API.
         """
         try:
-            bundle = DagBundlesManager().get_bundle(name=request.bundle_name, version=request.bundle_version)
+            bundle = DagBundlesManager().get_bundle(
+                name=request.bundle_name,
+                version=request.bundle_version,
+                version_data=request.version_data,
+            )
         except ValueError:
             self.log.error("Bundle %s no longer configured, skipping callback", request.bundle_name)
             return None
diff --git a/airflow-core/src/airflow/executors/workloads/callback.py b/airflow-core/src/airflow/executors/workloads/callback.py
index 04f26b8e787c1..a83deebc101e8 100644
--- a/airflow-core/src/airflow/executors/workloads/callback.py
+++ b/airflow-core/src/airflow/executors/workloads/callback.py
@@ -114,9 +114,13 @@ def make(
     ) -> ExecuteCallback:
         """Create an ExecuteCallback workload from a Callback ORM model."""
         if not bundle_info:
+            from airflow.models.dag_version import resolve_pinned_version_data
+
+            version_data = resolve_pinned_version_data(dag_run.created_dag_version, dag_run.bundle_version)
             bundle_info = BundleInfo(
                 name=dag_run.dag_model.bundle_name,
                 version=dag_run.bundle_version,
+                version_data=version_data,
             )
         fname = f"executor_callbacks/{dag_run.dag_id}/{dag_run.run_id}/{callback.id}"
 
diff --git a/airflow-core/src/airflow/executors/workloads/task.py b/airflow-core/src/airflow/executors/workloads/task.py
index 611457f88a957..6c4e0ffa7e466 100644
--- a/airflow-core/src/airflow/executors/workloads/task.py
+++ b/airflow-core/src/airflow/executors/workloads/task.py
@@ -102,13 +102,12 @@ def make(
 
         ser_ti = TaskInstanceDTO.model_validate(ti, from_attributes=True)
         if not bundle_info:
-            version_data = None
-            if ti.dag_version is not None and ti.dag_run.bundle_version is not None:
-                version_data = ti.dag_version.version_data
+            from airflow.models.dag_version import resolve_pinned_version_data
+
             bundle_info = BundleInfo(
                 name=ti.dag_model.bundle_name,
                 version=ti.dag_run.bundle_version,
-                version_data=version_data,
+                version_data=resolve_pinned_version_data(ti.dag_version, ti.dag_run.bundle_version),
             )
         fname = log_filename_template_renderer()(ti=ti)
 
diff --git a/airflow-core/src/airflow/jobs/scheduler_job_runner.py b/airflow-core/src/airflow/jobs/scheduler_job_runner.py
index df2abe2aabd06..bcfdcb665c2c3 100644
--- a/airflow-core/src/airflow/jobs/scheduler_job_runner.py
+++ b/airflow-core/src/airflow/jobs/scheduler_job_runner.py
@@ -97,7 +97,7 @@
     ConnectionTestState,
 )
 from airflow.models.dag import DagModel
-from airflow.models.dag_version import DagVersion
+from airflow.models.dag_version import DagVersion, resolve_pinned_version_data
 from airflow.models.dagbag import DBDagBag
 from airflow.models.dagbundle import DagBundleModel
 from airflow.models.dagrun import DagRun
@@ -1512,6 +1512,7 @@ def process_executor_events(
                         if ti.dag_version and ti.dag_run.bundle_version is not None
                         else ti.dag_run.bundle_version
                     )
+                    _version_data = resolve_pinned_version_data(ti.dag_version, ti.dag_run.bundle_version)
                     # Backfill dag_version_id for legacy tasks (Pydantic requires uuid.UUID).
                     if not _ensure_ti_has_dag_version_id(ti, session, cls.logger()):
                         continue
@@ -1519,6 +1520,7 @@ def process_executor_events(
                         filepath=ti.dag_model.relative_fileloc or "",
                         bundle_name=_bundle_name,
                         bundle_version=_bundle_version,
+                        version_data=_version_data,
                         ti=ti,
                         msg=msg,
                         task_callback_type=(
@@ -1561,6 +1563,9 @@ def process_executor_events(
                     _email_bundle_version = (
                         ti.dag_version.bundle_version if ti.dag_version else ti.dag_run.bundle_version
                     )
+                    _email_version_data = resolve_pinned_version_data(
+                        ti.dag_version, ti.dag_run.bundle_version
+                    )
                     # Backfill dag_version_id for legacy tasks (Pydantic requires uuid.UUID).
                     if not _ensure_ti_has_dag_version_id(ti, session, cls.logger()):
                         continue
@@ -1568,6 +1573,7 @@ def process_executor_events(
                         filepath=ti.dag_model.relative_fileloc or "",
                         bundle_name=_email_bundle_name,
                         bundle_version=_email_bundle_version,
+                        version_data=_email_version_data,
                         ti=ti,
                         msg=msg,
                         email_type="retry" if ti.is_eligible_to_retry() else "failure",
@@ -3068,6 +3074,9 @@ def _maybe_requeue_stuck_ti(self, *, ti, session, executor):
                         if ti.dag_version and ti.dag_run.bundle_version is not None
                         else ti.dag_run.bundle_version
                     )
+                    _stuck_version_data = resolve_pinned_version_data(
+                        ti.dag_version, ti.dag_run.bundle_version
+                    )
                     # Backfill dag_version_id for legacy tasks (Pydantic requires uuid.UUID).
                     # Note: we cannot use `continue` here because this method is not
                     # inside a loop.  If backfilling fails we simply skip the callback.
@@ -3076,6 +3085,7 @@ def _maybe_requeue_stuck_ti(self, *, ti, session, executor):
                             filepath=ti.dag_model.relative_fileloc or "",
                             bundle_name=_stuck_bundle_name,
                             bundle_version=_stuck_bundle_version,
+                            version_data=_stuck_version_data,
                             ti=ti,
                             msg=msg,
                             context_from_server=TIRunContext(
@@ -3539,6 +3549,7 @@ def _purge_task_instances_without_heartbeats(
                 if ti.dag_version and ti.dag_run.bundle_version is not None
                 else ti.dag_run.bundle_version
             )
+            _hb_version_data = resolve_pinned_version_data(ti.dag_version, ti.dag_run.bundle_version)
             # Backfill dag_version_id for legacy tasks (Pydantic requires uuid.UUID).
             if not _ensure_ti_has_dag_version_id(ti, session, self.log):
                 continue
@@ -3546,6 +3557,7 @@ def _purge_task_instances_without_heartbeats(
                 filepath=ti.dag_model.relative_fileloc or "",
                 bundle_name=_hb_bundle_name,
                 bundle_version=_hb_bundle_version,
+                version_data=_hb_version_data,
                 ti=ti,
                 msg=str(task_instance_heartbeat_timeout_message_details),
                 context_from_server=TIRunContext(
diff --git a/airflow-core/src/airflow/models/dag_version.py b/airflow-core/src/airflow/models/dag_version.py
index e6564a6da0668..678857a47728d 100644
--- a/airflow-core/src/airflow/models/dag_version.py
+++ b/airflow-core/src/airflow/models/dag_version.py
@@ -19,7 +19,7 @@
 
 import logging
 from datetime import datetime
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Any
 from uuid import UUID
 
 import sqlalchemy as sa
@@ -235,3 +235,21 @@ def get_version(
     def version(self) -> str:
         """A human-friendly representation of the version."""
         return f"{self.dag_id}-{self.version_number}"
+
+
+def resolve_pinned_version_data(
+    dag_version: DagVersion | None, bundle_version: str | None
+) -> dict[str, Any] | None:
+    """
+    Return a bundle version's ``version_data`` manifest, but only for pinned runs.
+
+    Mirrors the bundle-version pinning rule used when building task and callback
+    workloads: ``version_data`` is exposed only when the run is pinned
+    (``bundle_version`` is set) and a ``DagVersion`` is available, so the worker
+    initializes the bundle against the exact version the run used. Returns ``None``
+    for unpinned runs (which should follow the latest bundle state) and for legacy
+    rows without a ``DagVersion``.
+    """
+    if dag_version is not None and bundle_version is not None:
+        return dag_version.version_data
+    return None
diff --git a/airflow-core/src/airflow/models/dagrun.py b/airflow-core/src/airflow/models/dagrun.py
index 056151cefa1c1..d143daf9e5f9f 100644
--- a/airflow-core/src/airflow/models/dagrun.py
+++ b/airflow-core/src/airflow/models/dagrun.py
@@ -1449,12 +1449,18 @@ def produce_dag_callback(
             )
             relevant_ti = None
         if not execute:
+            from airflow.models.dag_version import resolve_pinned_version_data
+
+            # Only carry version_data for pinned runs so the callback initializes the bundle
+            # against the same version the run used.
+            version_data = resolve_pinned_version_data(self.created_dag_version, self.bundle_version)
             return DagCallbackRequest(
                 filepath=self.dag_model.relative_fileloc,
                 dag_id=self.dag_id,
                 run_id=self.run_id,
                 bundle_name=self.dag_model.bundle_name,
                 bundle_version=self.bundle_version,
+                version_data=version_data,
                 context_from_server=DagRunContext(
                     dag_run=self,
                     last_ti=relevant_ti,
diff --git a/airflow-core/src/airflow/models/trigger.py b/airflow-core/src/airflow/models/trigger.py
index 6fecd4d825f09..95e81fd2e23b1 100644
--- a/airflow-core/src/airflow/models/trigger.py
+++ b/airflow-core/src/airflow/models/trigger.py
@@ -566,12 +566,18 @@ def _submit_callback_if_necessary() -> None:
         if event.task_instance_state in (TaskInstanceState.SUCCESS, TaskInstanceState.FAILED):
             if task_instance.dag_model.relative_fileloc is None:
                 raise RuntimeError("relative_fileloc should not be None for a finished task")
+            from airflow.models.dag_version import resolve_pinned_version_data
+
+            version_data = resolve_pinned_version_data(
+                task_instance.dag_version, task_instance.dag_run.bundle_version
+            )
             request = TaskCallbackRequest(
                 filepath=task_instance.dag_model.relative_fileloc,
                 ti=task_instance,
                 task_callback_type=event.task_instance_state,
                 bundle_name=task_instance.dag_model.bundle_name,
                 bundle_version=task_instance.dag_run.bundle_version,
+                version_data=version_data,
             )
             log.info("Sending callback: %s", request)
             try:
diff --git a/airflow-core/tests/unit/callbacks/test_callback_requests.py b/airflow-core/tests/unit/callbacks/test_callback_requests.py
index 434223e37475f..9b85d61e5dba0 100644
--- a/airflow-core/tests/unit/callbacks/test_callback_requests.py
+++ b/airflow-core/tests/unit/callbacks/test_callback_requests.py
@@ -118,6 +118,33 @@ def test_is_failure_callback_property(
 
         assert request.is_failure_callback == expected_is_failure
 
+    def test_version_data_round_trips_and_defaults_none(self):
+        """version_data survives JSON serialization and defaults to None when omitted."""
+        version_data = {"schema_version": 1, "files": {"dags/my_dag.py": "ver123"}}
+        request = DagCallbackRequest(
+            filepath="filepath",
+            dag_id="fake_dag",
+            run_id="fake_run",
+            is_failure_callback=False,
+            bundle_name="testing",
+            bundle_version="abc123",
+            version_data=version_data,
+        )
+        result = DagCallbackRequest.from_json(request.to_json())
+        assert result.version_data == version_data
+
+        # Omitted -> defaults to None and round-trips as None.
+        unpinned = DagCallbackRequest(
+            filepath="filepath",
+            dag_id="fake_dag",
+            run_id="fake_run",
+            is_failure_callback=False,
+            bundle_name="testing",
+            bundle_version=None,
+        )
+        assert unpinned.version_data is None
+        assert DagCallbackRequest.from_json(unpinned.to_json()).version_data is None
+
 
 class TestDagRunContext:
     def test_dagrun_context_creation(self):
diff --git a/airflow-core/tests/unit/dag_processing/test_manager.py b/airflow-core/tests/unit/dag_processing/test_manager.py
index 4b55b6b2f1ee9..8ff1e46d52801 100644
--- a/airflow-core/tests/unit/dag_processing/test_manager.py
+++ b/airflow-core/tests/unit/dag_processing/test_manager.py
@@ -1375,6 +1375,7 @@ def test_collect_results_processes_remaining_files_when_one_persist_fails(self,
                             "filepath": "dag_callback_dag.py",
                             "bundle_name": "testing",
                             "bundle_version": None,
+                            "version_data": None,
                             "msg": None,
                             "dag_id": "dag_id",
                             "run_id": "run_id",
@@ -1967,7 +1968,28 @@ def test_prepare_callback_bundle_initializes_versioned_bundle(self, mock_bundle_
         bundle.initialize.assert_called_once()
 
     @mock.patch("airflow.dag_processing.manager.DagBundlesManager")
-    def test_prepare_callback_bundle_skips_initialize_for_unversioned_request(self, mock_bundle_manager):
+    def test_prepare_callback_bundle_forwards_version_data(self, mock_bundle_manager):
+        manager = DagFileProcessorManager(max_runs=1)
+        bundle = MagicMock(spec=BaseDagBundle)
+        bundle.supports_versioning = True
+        mock_bundle_manager.return_value.get_bundle.return_value = bundle
+
+        version_data = {"schema_version": 1, "files": {"dags/my_dag.py": "ver123"}}
+        request = DagCallbackRequest(
+            filepath="file1.py",
+            dag_id="dag1",
+            run_id="run1",
+            is_failure_callback=False,
+            bundle_name="testing",
+            bundle_version="some_commit_hash",
+            version_data=version_data,
+            msg=None,
+        )
+
+        manager.prepare_callback_bundle(request)
+        mock_bundle_manager.return_value.get_bundle.assert_called_once_with(
+            name="testing", version="some_commit_hash", version_data=version_data
+        )
         manager = DagFileProcessorManager(max_runs=1)
         bundle = MagicMock(spec=BaseDagBundle)
         bundle.supports_versioning = True
diff --git a/airflow-core/tests/unit/executors/test_workloads.py b/airflow-core/tests/unit/executors/test_workloads.py
index 63a249a36fd1b..1ef04477d081c 100644
--- a/airflow-core/tests/unit/executors/test_workloads.py
+++ b/airflow-core/tests/unit/executors/test_workloads.py
@@ -28,7 +28,7 @@
 from airflow.executors import workloads
 from airflow.executors.workloads import TaskInstance, TaskInstanceDTO, base as workloads_base
 from airflow.executors.workloads.base import BaseWorkloadSchema, BundleInfo
-from airflow.executors.workloads.callback import CallbackDTO, CallbackFetchMethod
+from airflow.executors.workloads.callback import CallbackDTO, CallbackFetchMethod, ExecuteCallback
 from airflow.executors.workloads.task import ExecuteTask
 from airflow.executors.workloads.types import state_class_for_key
 from airflow.models.callback import CallbackKey
@@ -250,3 +250,61 @@ def test_missing_dag_version_yields_none(self):
 
         assert workload.bundle_info.version == "abc123"
         assert workload.bundle_info.version_data is None
+
+
+class TestExecuteCallbackMakeVersionData:
+    """Tests for ExecuteCallback.make() threading version_data through BundleInfo."""
+
+    @staticmethod
+    def _make_mocks(bundle_version, version_data, *, has_created_dag_version=True):
+        """Build mock Callback + DagRun with the attributes ExecuteCallback.make() reads."""
+        from unittest.mock import Mock
+
+        callback = Mock()
+        callback.id = uuid4()
+        callback.fetch_method = CallbackFetchMethod.IMPORT_PATH
+        callback.data = {"path": "my_module.my_callback"}
+
+        dag_run = Mock()
+        dag_run.dag_id = "test_dag"
+        dag_run.run_id = "test_run"
+        dag_run.bundle_version = bundle_version
+        dag_run.dag_model.bundle_name = "test-bundle"
+        dag_run.dag_model.relative_fileloc = "dags/test_dag.py"
+        if has_created_dag_version:
+            dag_run.created_dag_version.version_data = version_data
+        else:
+            dag_run.created_dag_version = None
+
+        return callback, dag_run
+
+    def test_pinned_run_populates_version_data(self):
+        """When the run is pinned, version_data from created_dag_version flows to BundleInfo."""
+        version_data = {"schema_version": 1, "files": {"dags/my_dag.py": "ver123"}}
+        callback, dag_run = self._make_mocks(bundle_version="abc123", version_data=version_data)
+
+        workload = ExecuteCallback.make(callback=callback, dag_run=dag_run)
+
+        assert workload.bundle_info.version == "abc123"
+        assert workload.bundle_info.version_data == version_data
+
+    def test_unpinned_run_suppresses_present_version_data(self):
+        """An unpinned run must not expose version_data even when created_dag_version carries it."""
+        version_data = {"schema_version": 1, "files": {"dags/my_dag.py": "ver123"}}
+        callback, dag_run = self._make_mocks(bundle_version=None, version_data=version_data)
+
+        workload = ExecuteCallback.make(callback=callback, dag_run=dag_run)
+
+        assert workload.bundle_info.version is None
+        assert workload.bundle_info.version_data is None
+
+    def test_missing_created_dag_version_yields_none(self):
+        """A pinned run without a created_dag_version yields no version_data."""
+        callback, dag_run = self._make_mocks(
+            bundle_version="abc123", version_data=None, has_created_dag_version=False
+        )
+
+        workload = ExecuteCallback.make(callback=callback, dag_run=dag_run)
+
+        assert workload.bundle_info.version == "abc123"
+        assert workload.bundle_info.version_data is None
diff --git a/airflow-core/tests/unit/jobs/test_scheduler_job.py b/airflow-core/tests/unit/jobs/test_scheduler_job.py
index e2d5977eb86f7..eaa4ac9064aac 100644
--- a/airflow-core/tests/unit/jobs/test_scheduler_job.py
+++ b/airflow-core/tests/unit/jobs/test_scheduler_job.py
@@ -729,6 +729,7 @@ def test_process_executor_events_with_callback(
             ti=mock.ANY,
             bundle_name="dag_maker",
             bundle_version=None,
+            version_data=None,
             msg=f"Executor {executor} reported that the task instance "
             f"<TaskInstance: test_process_executor_events_with_callback.dummy_task test [queued] ti_id={ti1.id}> "
             "finished with state failed, but the task instance's state attribute is queued. "
diff --git a/airflow-core/tests/unit/models/test_dag_version.py b/airflow-core/tests/unit/models/test_dag_version.py
index ec600c7be66e3..def8a0a35127c 100644
--- a/airflow-core/tests/unit/models/test_dag_version.py
+++ b/airflow-core/tests/unit/models/test_dag_version.py
@@ -17,6 +17,7 @@
 from __future__ import annotations
 
 from datetime import timedelta
+from unittest import mock
 
 import pytest
 from sqlalchemy import func, select
@@ -181,3 +182,31 @@ def test_write_dag_without_version_data(self, dag_maker, session):
         retrieved = DagVersion.get_latest_version("test_no_version_data", session=session)
         assert retrieved.version_data is None
         assert retrieved.bundle_version == "abc123"
+
+
+class TestResolvePinnedVersionData:
+    """Unit tests for the resolve_pinned_version_data pin-guard helper."""
+
+    @pytest.mark.parametrize(
+        ("dag_version", "bundle_version", "expected"),
+        [
+            pytest.param(
+                mock.Mock(version_data={"schema_version": 1}),
+                "abc123",
+                {"schema_version": 1},
+                id="pinned-with-data",
+            ),
+            pytest.param(
+                mock.Mock(version_data={"schema_version": 1}),
+                None,
+                None,
+                id="unpinned-suppresses-present-data",
+            ),
+            pytest.param(None, "abc123", None, id="missing-dag-version"),
+            pytest.param(None, None, None, id="unpinned-and-missing"),
+        ],
+    )
+    def test_resolve_pinned_version_data(self, dag_version, bundle_version, expected):
+        from airflow.models.dag_version import resolve_pinned_version_data
+
+        assert resolve_pinned_version_data(dag_version, bundle_version) == expected
diff --git a/task-sdk/src/airflow/sdk/execution_time/schema/schema.json b/task-sdk/src/airflow/sdk/execution_time/schema/schema.json
index ae736e5d6621e..4f6e5065d6e5d 100644
--- a/task-sdk/src/airflow/sdk/execution_time/schema/schema.json
+++ b/task-sdk/src/airflow/sdk/execution_time/schema/schema.json
@@ -753,6 +753,19 @@
           ],
           "title": "Bundle Version"
         },
+        "version_data": {
+          "anyOf": [
+            {
+              "additionalProperties": true,
+              "type": "object"
+            },
+            {
+              "type": "null"
+            }
+          ],
+          "default": null,
+          "title": "Version Data"
+        },
         "msg": {
           "anyOf": [
             {
@@ -1651,6 +1664,19 @@
           ],
           "title": "Bundle Version"
         },
+        "version_data": {
+          "anyOf": [
+            {
+              "additionalProperties": true,
+              "type": "object"
+            },
+            {
+              "type": "null"
+            }
+          ],
+          "default": null,
+          "title": "Version Data"
+        },
         "msg": {
           "anyOf": [
             {
@@ -3859,6 +3885,19 @@
           ],
           "title": "Bundle Version"
         },
+        "version_data": {
+          "anyOf": [
+            {
+              "additionalProperties": true,
+              "type": "object"
+            },
+            {
+              "type": "null"
+            }
+          ],
+          "default": null,
+          "title": "Version Data"
+        },
         "msg": {
           "anyOf": [
             {